Ethyl 3-Cyano-2-mercapto-6-methylpyridine-4-carboxylate FAQ
Ethyl 3-Cyano-2-mercapto-6-methylpyridine-4-carboxylate FAQ
Ethyl 3-cyano-2-mercapto-6-methylpyridine-4-carboxylate is a multifunctional pyridine-based building block bearing a free thiol, a nitrile, and an ethyl ester group, making it a versatile synthetic intermediate for heterocyclic and medicinal chemistry research.
- Product Name
- Ethyl 3-cyano-2-mercapto-6-methylpyridine-4-carboxylate
- SKU
- E698827
- Functional Groups
- Thiol (–SH), nitrile (–CN), ethyl ester (–COOEt), methyl-substituted pyridine ring
- Primary Use
- Synthetic intermediate and building block for heterocyclic compound synthesis
- Storage Recommendation
- Store in a cool, dry, well-ventilated area away from oxidising agents; seal tightly after use
- Supplier
- Aladdin Scientific (SKU E698827)
What Is Ethyl 3-Cyano-2-mercapto-6-methylpyridine-4-carboxylate?
Ethyl 3-cyano-2-mercapto-6-methylpyridine-4-carboxylate is a pyridine derivative featuring three reactive functional groups on a single aromatic ring: a free thiol (–SH) at the 2-position, a nitrile (–CN) at the 3-position, and an ethyl ester (–COOEt) at the 4-position, with a methyl group at the 6-position. This combination of orthogonal reactivity makes the compound a highly sought-after building block in the design and synthesis of diverse heterocyclic scaffolds, including thienopyridines, pyrido-fused systems, and other sulfur-containing heterocycles relevant to pharmaceutical and agrochemical research.
Key Chemical Properties and Handling
The thiol group in this compound is susceptible to oxidation, which can lead to disulfide formation under aerobic conditions. Researchers should handle the reagent under inert atmosphere (nitrogen or argon) when possible, particularly for long-term storage or when dissolved in solution. The nitrile and ester functionalities are stable under mild conditions but can participate in condensation, cyclisation, and nucleophilic addition reactions under appropriate reagents and conditions. The compound should be weighed in a well-ventilated fume hood owing to the potential for volatile thiol-containing decomposition products. Contact with strong oxidising agents should be avoided.
Typical Synthetic Applications
This building block is commonly employed in the construction of fused heterocyclic systems. The thiol group can react with alpha-halo carbonyl compounds, activated alkenes, or electrophiles to form thioether linkages or initiate ring-closure sequences. The nitrile group can be converted to amidines, tetrazoles, or participate in Knoevenagel-type condensations. The ethyl ester can be hydrolysed, transesterified, or converted to amides and other carbonyl derivatives. The combination of these features enables rapid access to polyfunctionalised pyridine-fused ring systems that are of interest in drug discovery programmes targeting a range of biological pathways.
Storage and Stability Guidelines
To preserve reagent integrity, store Ethyl 3-cyano-2-mercapto-6-methylpyridine-4-carboxylate (SKU E698827) in a tightly sealed container in a cool, dry location away from light and moisture. Thiol-containing compounds are particularly prone to aerial oxidation; therefore, minimising headspace in storage vessels and using inert gas blankets is recommended for opened containers. Check the compound for discolouration or solidification that may indicate degradation before use. If purity assurance is critical to your experiment, consider verifying purity by HPLC or NMR prior to use.
Ordering and Availability
Ethyl 3-cyano-2-mercapto-6-methylpyridine-4-carboxylate is available from Aladdin Scientific under SKU E698827. Please contact your regional Aladdin Scientific representative or visit the Aladdin Scientific website to confirm current stock levels, available pack sizes, and pricing. For bulk or custom quantity enquiries, our sales team can provide quotations tailored to your laboratory's needs. All orders are subject to Aladdin Scientific's standard terms and conditions regarding payment, shipping, and returns.
Frequently asked questions
What functional groups are present in Ethyl 3-cyano-2-mercapto-6-methylpyridine-4-carboxylate?
The compound contains a free thiol (–SH) at the 2-position, a nitrile (–CN) at the 3-position, an ethyl ester (–COOEt) at the 4-position, and a methyl group at the 6-position of the pyridine ring. These orthogonally reactive groups make it suitable for a wide range of synthetic transformations.
How should I store Ethyl 3-cyano-2-mercapto-6-methylpyridine-4-carboxylate to prevent degradation?
Store the compound in a tightly sealed container in a cool, dry, well-ventilated area away from oxidising agents and direct light. For opened containers, minimise headspace and consider using an inert gas (nitrogen or argon) blanket to reduce oxidation of the thiol group. Verify purity before critical experiments.
What are the primary synthetic uses of this compound?
Ethyl 3-cyano-2-mercapto-6-methylpyridine-4-carboxylate is widely used as a building block for constructing fused heterocyclic systems such as thienopyridines and related scaffolds. The thiol, nitrile, and ester groups each provide distinct handles for further chemical elaboration, including S-alkylation, cyclisation, amide formation, and nitrile conversion to amidines or tetrazoles.
Is Ethyl 3-cyano-2-mercapto-6-methylpyridine-4-carboxylate air-sensitive?
Yes, the free thiol group renders the compound susceptible to oxidation by atmospheric oxygen, which can lead to disulfide formation and reduced purity over time. It is advisable to handle and store the compound under inert conditions where possible, especially when dissolved in solution.
How can I order Ethyl 3-cyano-2-mercapto-6-methylpyridine-4-carboxylate from Aladdin Scientific?
You can order this compound directly from Aladdin Scientific using SKU E698827 through the Aladdin Scientific website or by contacting your regional sales representative. For bulk quantities or special packaging requirements, please reach out to the sales team for a custom quotation.
References
- General principles of thiol reactivity and heterocyclic building block synthesis — standard organic chemistry reference; specific literature not identified in source material.
- Aladdin Scientific product listing for Ethyl 3-cyano-2-mercapto-6-methylpyridine-4-carboxylate, SKU E698827.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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